Water → (6R,7aS)-6-(tert-Butyl-diphenyl-silanyloxy)-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one

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Reaction Conditions

Reaction Steps

t-BuOK (1.0 g, 8.9 mmol) was added to a solution of (2S,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid (4-trifluoromethoxy-phenyl)-amide (2.0 g, 3.6 mmol) in anhydrous THF (50 mL) at 0° C. The mixture was stirred for 15 minutes at 0° C. Then tosyl-chloride (0.88 g, 4.6 mmol) was added to the mixture, and the mixture was stirred for 30 minutes at 0° C. The mixture was poured into water (50 mL), extracted with ethyl acetate (3×50 mL). The organic layers was combined, washed with brine (50 mL), dried over anhydrous sodium sulphate, filtered and concentrated. The residue was purified by silica-gel column chromatography (petroleum ether/ethyl acetate=10:1) to give 1.6 g (83%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 7.68-7.63 (m, 4H), 7.58 (d, 2H, J=9.3 Hz), 7.50-7.39 (m, 6H), 7.19 (d, 2H, J=9.0 Hz), 4.56 (t, 1H, J=5.1 Hz), 4.30-4.22 (m, 1H), 4.04 (t, 1H, J=8.4 Hz), 3.86 (dd, 1H, J1=12.6 Hz, J2=5.7), 3.67 (dd, 1H, J1=9.3 Hz, J2=2.4 Hz), 3.18 (d, 1H, J=12.6 Hz), 2.07 (dd, 1H, J1=12.6, J2=5.4), 1.46-1.37 (m, 1H), 1.11 (s, 9H).

Provenance & Evidence